WO2010042315A3 - Process for producing cumene - Google Patents

Process for producing cumene Download PDF

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Publication number
WO2010042315A3
WO2010042315A3 PCT/US2009/057949 US2009057949W WO2010042315A3 WO 2010042315 A3 WO2010042315 A3 WO 2010042315A3 US 2009057949 W US2009057949 W US 2009057949W WO 2010042315 A3 WO2010042315 A3 WO 2010042315A3
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WO
WIPO (PCT)
Prior art keywords
stream
benzene
reaction zone
hydrogen
feed stream
Prior art date
Application number
PCT/US2009/057949
Other languages
French (fr)
Other versions
WO2010042315A2 (en
Inventor
Shyh-Yuan Henry Hwang
Dana E. Johnson
Joseph C. Peters
Chung-Ming Chi
Kevin J. Fallon
Francis A. Demers
Original Assignee
Badger Licensing, Llc
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Badger Licensing, Llc filed Critical Badger Licensing, Llc
Priority to US13/119,789 priority Critical patent/US20110201858A1/en
Priority to CN2009801393096A priority patent/CN102171168A/en
Priority to JP2011530112A priority patent/JP2012504622A/en
Priority to BRPI0920691A priority patent/BRPI0920691A2/en
Priority to EP09792873A priority patent/EP2346798A2/en
Publication of WO2010042315A2 publication Critical patent/WO2010042315A2/en
Publication of WO2010042315A3 publication Critical patent/WO2010042315A3/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
    • C07C2/86—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by condensation between a hydrocarbon and a non-hydrocarbon
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C409/00—Peroxy compounds
    • C07C409/02—Peroxy compounds the —O—O— group being bound between a carbon atom, not further substituted by oxygen atoms, and hydrogen, i.e. hydroperoxides
    • C07C409/04—Peroxy compounds the —O—O— group being bound between a carbon atom, not further substituted by oxygen atoms, and hydrogen, i.e. hydroperoxides the carbon atom being acyclic
    • C07C409/08—Compounds containing six-membered aromatic rings
    • C07C409/10—Cumene hydroperoxide
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
    • C07C15/02—Monocyclic hydrocarbons
    • C07C15/085—Isopropylbenzene
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
    • C07C2/54—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition of unsaturated hydrocarbons to saturated hydrocarbons or to hydrocarbons containing a six-membered aromatic ring with no unsaturation outside the aromatic ring
    • C07C2/64—Addition to a carbon atom of a six-membered aromatic ring
    • C07C2/66—Catalytic processes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
    • C07C2/86—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by condensation between a hydrocarbon and a non-hydrocarbon
    • C07C2/862—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by condensation between a hydrocarbon and a non-hydrocarbon the non-hydrocarbon contains only oxygen as hetero-atoms
    • C07C2/864—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by condensation between a hydrocarbon and a non-hydrocarbon the non-hydrocarbon contains only oxygen as hetero-atoms the non-hydrocarbon is an alcohol
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
    • C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
    • C07C29/143—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of ketones
    • C07C29/145—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of ketones with hydrogen or hydrogen-containing gases
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
    • C07C37/08—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by decomposition of hydroperoxides, e.g. cumene hydroperoxide
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
    • C07C39/02—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring monocyclic with no unsaturation outside the aromatic ring
    • C07C39/04—Phenol
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C407/00—Preparation of peroxy compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
    • C07C45/53—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition of hydroperoxides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2529/00—Catalysts comprising molecular sieves
    • C07C2529/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites, pillared clays
    • C07C2529/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
    • C07C2529/08—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of the faujasite type, e.g. type X or Y
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2529/00—Catalysts comprising molecular sieves
    • C07C2529/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites, pillared clays
    • C07C2529/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
    • C07C2529/18—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of the mordenite type
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2529/00—Catalysts comprising molecular sieves
    • C07C2529/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites, pillared clays
    • C07C2529/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
    • C07C2529/40—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of the pentasil type, e.g. types ZSM-5, ZSM-8 or ZSM-11
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2529/00—Catalysts comprising molecular sieves
    • C07C2529/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites, pillared clays
    • C07C2529/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
    • C07C2529/65—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of the ferrierite type, e.g. types ZSM-21, ZSM-35 or ZSM-38
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2529/00—Catalysts comprising molecular sieves
    • C07C2529/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites, pillared clays
    • C07C2529/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
    • C07C2529/70—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of types characterised by their specific structure not provided for in groups C07C2529/08 - C07C2529/65

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

In a process for producing cumene from acetone and benzene, a feed stream comprising acetone is contacted with hydrogen in the presence of a hydrogenation catalyst in a first reaction zone under hydrogenation conditions sufficient to convert at least part of the acetone to isopropanol and produce a first liquid effluent stream rich in isopropanol and a first vapor stream rich in unreacted hydrogen. Benzene is then added to at least part of the first liquid effluent stream, without intermediate purification of the first liquid effluent stream, and optionally to at least part of the first vapor stream, to form a second feed stream. The second feed stream is then contacted with an alkylation catalyst in a second reaction zone separate from the first reaction zone under alkylation conditions sufficient to maintain at least part of the second feed stream in the liquid phase and to cause at least part of the isopropanol in the second feed stream to react with the benzene to form cumene and water and produce a second effluent stream comprising at least cumene, water and unreacted benzene. Hydrogen is separated from the first vapor stream and/or the second effluent stream. At least part of the hydrogen is recycled to the first reaction zone and/or purged from the system.
PCT/US2009/057949 2008-10-06 2009-09-23 Process for producing cumene WO2010042315A2 (en)

Priority Applications (5)

Application Number Priority Date Filing Date Title
US13/119,789 US20110201858A1 (en) 2008-10-06 2009-09-23 Process for producing cumene
CN2009801393096A CN102171168A (en) 2008-10-06 2009-09-23 Process for producing cumene
JP2011530112A JP2012504622A (en) 2008-10-06 2009-09-23 Cumene production process
BRPI0920691A BRPI0920691A2 (en) 2008-10-06 2009-09-23 process for cumene production
EP09792873A EP2346798A2 (en) 2008-10-06 2009-09-23 Process for producing cumene

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US10306608P 2008-10-06 2008-10-06
US61/103,066 2008-10-06
US10754808P 2008-10-22 2008-10-22
US61/107,548 2008-10-22

Publications (2)

Publication Number Publication Date
WO2010042315A2 WO2010042315A2 (en) 2010-04-15
WO2010042315A3 true WO2010042315A3 (en) 2010-06-03

Family

ID=41785934

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2009/057949 WO2010042315A2 (en) 2008-10-06 2009-09-23 Process for producing cumene

Country Status (8)

Country Link
US (1) US20110201858A1 (en)
EP (1) EP2346798A2 (en)
JP (1) JP2012504622A (en)
KR (1) KR20110082156A (en)
CN (1) CN102171168A (en)
BR (1) BRPI0920691A2 (en)
SG (1) SG195586A1 (en)
WO (1) WO2010042315A2 (en)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
TWI458695B (en) 2008-10-06 2014-11-01 Badger Licensing Llc Process for producing cumene
US8702971B2 (en) * 2010-03-31 2014-04-22 Uop Llc Process and apparatus for alkylating and hydrogenating a light cycle oil
CN104520258A (en) * 2012-07-26 2015-04-15 巴杰许可有限责任公司 Process for producing cumene
US9593056B2 (en) 2012-12-11 2017-03-14 Exxonmobil Chemical Patents Inc. Process for producing cumene with alkylation effluent recycle
IT201900015066A1 (en) 2019-08-27 2021-02-27 Versalis Spa PROCEDURE FOR THE TREATMENT OF POLYALKYLAROMATIC HYDROCARBONS.
CN113384910B (en) * 2021-07-19 2022-04-22 南京工程学院 Multi-effect cumene reaction rectification device and method combined with heat pump

Citations (2)

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EP0371738A2 (en) * 1988-11-28 1990-06-06 Mitsui Petrochemical Industries, Ltd. Preparation of phenol through cumene
WO2008102664A1 (en) * 2007-02-23 2008-08-28 Mitsui Chemicals, Inc. Process for producing alkylated aromatic compound

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EP0371738A2 (en) * 1988-11-28 1990-06-06 Mitsui Petrochemical Industries, Ltd. Preparation of phenol through cumene
WO2008102664A1 (en) * 2007-02-23 2008-08-28 Mitsui Chemicals, Inc. Process for producing alkylated aromatic compound
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Also Published As

Publication number Publication date
SG195586A1 (en) 2013-12-30
WO2010042315A2 (en) 2010-04-15
CN102171168A (en) 2011-08-31
US20110201858A1 (en) 2011-08-18
KR20110082156A (en) 2011-07-18
JP2012504622A (en) 2012-02-23
EP2346798A2 (en) 2011-07-27
BRPI0920691A2 (en) 2015-12-29

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